Methyl 2-amino-5-fluoro-3-hydroxybenzoate → Methyl 2-amino-6-fluorobenzoxazole-4-carboxylate

Participants

Reaction Steps

To a solution of di-(1H-imidazole-1-yl)methanamine (1.05 g, 6.52 mmol) in THF (30 mL) was added methyl-2-amino-5-fluoro-3-hydroxybenzoate (0.96 g, 5.22 mmol) at room temperature and the resulting reaction mixture was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford methyl 2-amino-6-fluorobenzoxazole-4-carboxylate (0.95 g, 87%) as a yellow solid. 1H NMR and MS consistent.

Provenance & Evidence